Vacation rentals in Siesta Key

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Popular amenities for Siesta Key vacation rentals

Stay near Siesta Key's top sights

The Cottage68 locals recommend
Phillippi Estate Park17 locals recommend
PARASAIL SIESTA24 locals recommend
Siesta Beach Pavillion3 locals recommend
Siesta Key Oyster Bar167 locals recommend
South Lido Key Beach Park on the Gulf25 locals recommend

Condo rentals in Siesta Key

Guest favorite
Condo in Siesta Key
Bright and Beachy - Steps to the Water!
Apr 8 – 15
$328 per night
4.92 out of 5 average rating, 178 reviews
Superhost
Condo in Siesta Key
Private Beach Siesta Key Resort Jamaica Royale
Nov 24 – Dec 1
$499 per night
4.88 out of 5 average rating, 121 reviews
Guest favorite
Condo in Siesta Key
Sea Club 2 Condo Siesta Key
Jun 16 – 23
$180 per night
4.9 out of 5 average rating, 200 reviews
Guest favorite
Condo in Longboat Key
Cute Condo with a Stunning View!
Sep 9 – 16
$236 per night
4.97 out of 5 average rating, 146 reviews
Guest favorite
Condo in Siesta Key
[Beach Elements] pool view + private beach & bikes
Aug 9 – 16
$339 per night
4.8 out of 5 average rating, 278 reviews
Guest favorite
Condo in Siesta Key
Steps away from beach and village! #1 in Siesta!
Nov 21 – 28
$273 per night
4.93 out of 5 average rating, 177 reviews
Guest favorite
Condo in Siesta Key
New: Cozy 1BR Beach Condo on Siesta Key!!!
Aug 15 – 22
$150 per night
4.83 out of 5 average rating, 186 reviews
Guest favorite
Condo in Siesta Key
Cozy Siesta Key studio 5 minute walk to Village
Feb 23 – Mar 2
$288 per night
4.9 out of 5 average rating, 147 reviews

House rentals in Siesta Key

Guest favorite
Home in Sarasota
5 minutes to private Siesta Key Beach + 2 pools
Nov 25 – Dec 2
$320 per night
4.87 out of 5 average rating, 128 reviews
Guest favorite
Home in Sarasota
Your private retreat near Siesta Key Beach.
Sep 7 – 14
$289 per night
4.97 out of 5 average rating, 200 reviews
Guest favorite
Home in Siesta Key
Siesta Beach House
Jan 22 – 29
$299 per night
4.89 out of 5 average rating, 138 reviews
Guest favorite
Home in Sarasota
☀Coastal Gem☀Heated pool & amazing location!☀
Apr 23 – 30
$277 per night
4.94 out of 5 average rating, 292 reviews
Superhost
Home in Siesta Key
Sea Club II Garden House
Oct 23 – 30
$321 per night
4.91 out of 5 average rating, 117 reviews
Guest favorite
Home in Sarasota
Renovated Cozy Cottage "The Nest" Close to SIESTA
Jun 2 – 9
$149 per night
4.92 out of 5 average rating, 116 reviews
Guest favorite
Home in Sarasota
Gorgeous Home / Heated Pool and Spa
Dec 12 – 19
$281 per night
4.97 out of 5 average rating, 104 reviews
Guest favorite
Home in Sarasota
Beautiful 3 Bd, 2 bth Pool Home Near Siesta Key!
Jun 25 – Jul 2
$275 per night
4.98 out of 5 average rating, 128 reviews

Siesta Key beach vacation rentals

Guest favorite
Cottage in Siesta Key
Siesta Key Cozy Cottage across from the beach!
Jul 18 – 25
$261 per night
4.88 out of 5 average rating, 137 reviews
Superhost
Cottage in Siesta Key
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Oct 31 – Nov 7
$379 per night
4.88 out of 5 average rating, 210 reviews
Guest favorite
Condo in Siesta Key
Amazing beach view! Entire unit renovated!
Sep 19 – 26
$197 per night
5.0 out of 5 average rating, 17 reviews
Guest favorite
Condo in Siesta Key
NO Stairs, beachfront & short walk to the village!
Jan 28 – Feb 4
$686 per night
4.91 out of 5 average rating, 80 reviews
Guest favorite
Condo in Siesta Key
Palm Bay Club Most Desirable Spot on Siesta Key!
Jan 23 – 30
$432 per night
4.98 out of 5 average rating, 61 reviews
Guest favorite
Condo in Siesta Key
2 BR condo in Siesta Key w/ Private beach access
Oct 3 – 10
$235 per night
4.97 out of 5 average rating, 33 reviews
Guest favorite
Home in Siesta Key
Beachfront 180-Degree View, Walk to Village!
Jun 1 – 8
$500 per night
5.0 out of 5 average rating, 18 reviews
Guest favorite
Cottage in Siesta Key
Surf Shack- Walk to Village/Boat Dock Included
Jul 23 – 30
$125 per night
4.94 out of 5 average rating, 66 reviews

Quick stats about vacation rentals in Siesta Key

Total rentals

1.6K properties

Rentals with dedicated workspaces

680 properties have a dedicated workspace

Rentals with a pool

1.2K properties have a pool

Pet-friendly rentals

340 properties allow pets

Family-friendly rentals

1.3K properties are a good fit for families

Total number of reviews

28K reviews

Your guide to Siesta Key

All About Siesta Key

Siesta Key is an eight-mile-long barrier island off the coast of Sarasota, known for its soft quartz beaches, turquoise waters, and abundance of marine life. Due to its location on the western Florida shoreline in the balmy waters of the Gulf of Mexico, the island experiences ideal conditions year-round for swimming, paddling, and watersports. This small coastal community offers a host of recreational opportunities outside of the beach as well. Wander the Siesta Key Village, where you can find the many live music venues, boutique art shops, and souvenir vendors scattered throughout the small but lively downtown area. Check out one of the weekly farmer’s markets, spend an afternoon picking through the gift shops, or just lounge one the one of the white-sand beaches waiting for the sun to set over the Gulf.


The best time to stay in a vacation rental in Siesta Key

Thanks to the island's location in the Gulf of Mexico, weather conditions and water temperatures are favorable for most of the year. Beginning in March, temperatures start to rise, with averages peaking around mid October. You can expect heat and humidity at your Siesta Key rental during this period, but gulf stream breezes help keep things cool. Weekly farmers markets, a musical festival, and a fireworks show are just a few of the notable events happening through the summer season.

In winter, temperatures see a marginal decrease, with January and February being the coldest months. However, many still find both the air and water temperatures suitable for swimming. The winter also happens to be when many of the area’s art festivals take place. Check out the Chalk Art Festival towards the end of October or the sand sculpture competition in November where you can take sculpting classes and vote on your favorite piece of art.


Top things to do in Siesta Key

Point of Rocks

One of the best snorkeling sites on Siesta Key, this limestone rock outcropping is home to abundant marine life and migratory bird populations. Calm waters and clear conditions make this a perfect place for beginners and experienced snorkelers alike. Expect to see schools of tropical fish, crabs, ocean sponges, and manatees during the summer. You may even get lucky and spot some of the area’s resident dolphins.

Siesta Key Drum Circle

The Siesta Key drum circle is a weekly tradition held on Sundays at Englewood and Siesta beaches throughout the year. Beginning about an hour before sunset, local artists and dancers kick off an evening of music and dancing. Large crowds gather to watch the festivities as onlookers are encouraged to dance or grab a drum and beat along.

Deep-sea fishing

Sandwiched between the vast Gulf of Mexico and Roberts Bay, Siesta Key is a year-round fishing destination. The reefs attract cobia and grouper, and if you venture further out you’ll be rewarded with tuna and wahoo. July is peak season for red snapper, while the fall bait migration off the Florida coast is a big draw for anglers from October onward.

Frequently Asked Questions

  • How is the weather in Siesta Key?

    Siesta Key enjoys a tropical climate with warm weather throughout the year. Summer temperatures can rise up to 90°F (32°C) while winter temperatures rarely drop below 50°F (10°C). The island gets a significant amount of rainfall, especially during the summer months.

  • What are some of the best things to do in Siesta Key?

    Activities in Siesta Key often revolve around its beautiful beaches, where you can swim, sunbathe, or play beach volleyball. You can also explore the local shops and restaurants in Siesta Village, or take a boat tour to spot dolphins.

  • What is the best time of year to visit Siesta Key?

    The most popular time to visit Siesta Key is during the winter and spring months when the weather is warm and comfortable. A notable local event is the Siesta Key Crystal Classic, an international sand sculpting festival that takes place every November.

  • What are the best places to stay in Siesta Key?

    Popular areas to stay in Siesta Key include Siesta Village for its proximity to dining and shopping, Crescent Beach for its quiet atmosphere, and Turtle Beach for its family-friendly environment.

  • What are the best places to visit in Siesta Key?

    Siesta Key is known for its stunning beaches such as Siesta Beach and Turtle Beach. You might also find exploring the Siesta Key Village and Point of Rocks interesting. The latter is a limestone formation on Crescent Beach attracting snorkeling enthusiasts.

  • What are some hiking trails in Siesta Key?

    While Siesta Key is more known for its beautiful beaches, you can still explore walking trails such as the Palmer Point Beach trail or Turtle beach trail. These paths provide an opportunity to enjoy the island's natural beauty and spot local wildlife.

  • What are some family activities to do in Siesta Key?

    Families can have fun exploring the Siesta Key beaches, perfect for swimming and building sandcastles. The Siesta Key Water Sports provide opportunities to engage in safe marine activities. For nature lovers, the Siesta Key Marina has dolphin watching tours.

  • What are some of the best day trip ideas in Siesta Key?

    Popular day trips from Siesta Key include visiting the vibrant city of Sarasota, which has a lively arts scene, or exploring the Myakka River State Park, known for its diverse wildlife and hiking trails.

  • What types of vacation rentals are available in Siesta Key?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Siesta Key. From over 790 condo rentals to over 400 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • Are there vacation rentals with a dedicated workspace in Siesta Key?

    Yes! Work meets play with ease at over 680 vacation rentals in Siesta Key featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Sarasota County
  5. Siesta Key